4-{[5-amino-1-({1-[(3-carbamoyl-1-{[1-(2-{[1-({1-[(1-carboxy-2-hydroxypropyl)carbamoyl]-2-methylpropyl}carbamoyl)-3-methylbutyl]carbamoyl}pyrrolidin-1-yl)-3-hydroxy-1-oxobutan-2-yl]carbamoyl}propyl)carbamoyl]-2-hydroxyethyl}carbamoyl)pentyl]carbamoyl}-4-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid

• ChemBase ID: 105495
• Molecular Formular: C77H120N18O26S
• Molecular Mass: 1745.9467
• Monoisotopic Mass: 1744.83418705
• SMILES: CSCCC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(N)Cc1ccc(O)cc1)C(=O)NC(C(C)O)C(=O)NC(CO)C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CO)C(=O)NC(CCC(=O)N)C(=O)NC(C(C)O)C(=O)N1CCCC1C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)O
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)C(O)C)C(C)C)CC(C)C)C(O)C)CCC(=O)N)CO)NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)N)CCSC)CO)CCC(=O)O
• InChI: InChI=1S/C77H120N18O26S/c1-38(2)31-51(70(113)91-60(39(3)4)74(117)94-63(42(7)100)77(120)121)88-73(116)55-18-14-29-95(55)76(119)62(41(6)99)93-67(110)48(23-25-56(80)102)85-71(114)53(36-96)89-65(108)47(17-12-13-28-78)84-66(109)49(24-26-59(105)106)86-72(115)54(37-97)90-75(118)61(40(5)98)92-68(111)50(27-30-122-8)87-69(112)52(33-43-15-10-9-11-16-43)83-58(104)35-81-57(103)34-82-64(107)46(79)32-44-19-21-45(101)22-20-44/h9-11,15-16,19-22,38-42,46-55,60-63,96-101H,12-14,17-18,23-37,78-79H2,1-8H3,(H2,80,102)(H,81,103)(H,82,107)(H,83,104)(H,84,109)(H,85,114)(H,86,115)(H,87,112)(H,88,116)(H,89,108)(H,90,118)(H,91,113)(H,92,111)(H,93,110)(H,94,117)(H,105,106)(H,120,121)
• InChIKey: NXSIJWJXMWBCBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[5-amino-1-({1-[(3-carbamoyl-1-{[1-(2-{[1-({1-[(1-carboxy-2-hydroxypropyl)carbamoyl]-2-methylpropyl}carbamoyl)-3-methylbutyl]carbamoyl}pyrrolidin-1-yl)-3-hydroxy-1-oxobutan-2-yl]carbamoyl}propyl)carbamoyl]-2-hydroxyethyl}carbamoyl)pentyl]carbamoyl}-4-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid
• IUPAC Traditional name: 4-{[5-amino-1-({1-[(3-carbamoyl-1-{[1-(2-{[1-({1-[(1-carboxy-2-hydroxypropyl)carbamoyl]-2-methylpropyl}carbamoyl)-3-methylbutyl]carbamoyl}pyrrolidin-1-yl)-3-hydroxy-1-oxobutan-2-yl]carbamoyl}propyl)carbamoyl]-2-hydroxyethyl}carbamoyl)pentyl]carbamoyl}-4-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid
• Synonyms: β-Lipotropin 61-76); Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr; α-ENDORPHIN

Database IDs

• CAS Number: 59004-96-5
• PubChem SID: 162092385
• PubChem CID: 16133219

CALCULATED PROPERTIES

• Acid pKa: 3.1644597
• H Acceptors: 28
• H Donor: 25
• LogD (pH = 5.5): -13.844905
• LogD (pH = 7.4): -13.994407
• Log P: -13.8454485
• Molar Refractivity: 431.3265 cm^3
• Polarizability: 169.79964 Å^3
• Polar Surface Area: 718.82 Å^2
• Rotatable Bonds: 55
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C

REFERENCES

• Guillemin, C., R. Acad. Sci. Paris, Ser. D. , 282 : 783 (1976).